Emily's First
by CrossOverToThisSide
Summary: One shot. Set about a week after Emily admits to Ali that she and Ben never had sex. Alison teaches Emily how to touch herself after Emily admits she's never had an orgasm. VERY NSFW.
1. Chapter 1

Emily's hair was still wet from the shower, and she was tucked under her sheets wearing an oversized tee. She was lying on her side, the phone pressed between her ear and the pillow. She had been switching positions trying to get comfortable as she talked to Ali for the last forty-five minutes. It was late on a school night, and even though they had most of their classes together, and had spent the whole evening together at Hannah's, it seems like the conversation would never end. Emily loved when Alison singled her out, and this past week she was definitely receiving extra attention. It all started after that rumor that she slept with Ben. She would never do it so soon, and was definitely not ready, but she would be eventually, so who cares about a harmless rumor? Most of the conversation was Alison gossiping, and even though Emily didn't feel completely comfortable doing that, Ali was making her laugh and she didn't want the phone call to end. Suddenly they went from talking about a senior boy's virginity to hers, and then about the rumor again,

"So, I don't get it, Em. How come you haven't slept with Ben?"

Emily was wary because Alison never just innocently asked a question. She could tell by the tone of her voice there was more behind it.

"I don't know. I'm just not ready. I want to be, but I'm not."

Ali wasn't satisfied with the same answer she had been getting. "I can tell something's up. Tell me the truth. I won't tell. I promise." Alison's voice was sticky sweet. She dragged out the word promise in her most reassuring tone.

Emily could hear the smile in Alison's voice. She hadn't told the other girls that she was lying about her and Ben, and so Emily thought maybe she could trust telling Ali more. Even though it made her a little uncomfortable. She'd never really said any of these things out loud.

"Okay, if I tell you you can't tell a soul. None of the girls. No one."

Alison was practically squirming with delight at getting another secret from Emily. Sometimes she thought she had her figured out. And sometimes she wasn't so sure. "Duh, Emily. I haven't told that you're still a virgin have I?" Her voice taunting - daring Emily to continue.

"Okay." Emily took a deep breath. "I don't actually know what to do. I mean, I know how it works mechanically," She said the last sentence super fast, and then went on. "I just don't know if it will feel good. I've heard it hurts."

Alison rolled her eyes, expecting a different answer. Her tone was annoyed when she said, "Just tell him to warm you up first. Show him what you do to yourself if he doesn't know."

Emily started to squirm a little. Talking about this stuff out loud made her really uncomfortable. Especially because she was talking to Alison.

"That's just it, Ali. I don't do anything to myself." Emily held her breath waiting for Alison's response.

Alison laughed. "C'mon Em, it's just me. I mean, we all get down in the sheets sometimes. You can be honest."

Emily started to get a little defensive. "I am being honest, Ali. I've never done it."

The smile dropped from Alison's face when she realized it wasn't an act. Sweet, innocent Emily had never touched herself before. "Wait, so that means you've never...had an orgasm." Ali whispered the last part and glanced at her closed door.

Emily shut her eyes in embarrassment. "I guess not, no."

"Oh, trust me, you would know."

Emily's heart was pounding in her chest. She worked her nerve up before asking in a quiet voice. "What does it feel like?"

Ali quirked an eyebrow, "How about I tell you what to do, and you feel it for yourself?" She surprised even herself at the suggestion. But this was just too good for her to not stay involved. She loved the idea of being the one to show Emily the ropes.

Emily let out a little gasp, not expecting Alison to say something like that. Her hands were shaking a little. Was this really happening? Was Alison seriously saying she would teach her to...touch herself?

"I can't do that. Not on the phone with you. No way." Emily's voice sounded shocked.

"Oh, don't be such a prude. We're both girls. It's not a big deal." Alison said the word prude in a biting tone that made Emily feel stupid.

She relented, "Okay, maybe. But you have to promise you'll never tell anyone, Ali. I mean it. This is so embarrassing."

"Chill, Emily." Alison laughed a little before saying, "So what are you wearing?"

Emily didn't find her joking at her expense very funny. "Cut it out. I'm not going to do anything if you make fun of me the whole time."

"Okay. I'll be serious. But seriously, you need to have easy access. So if you're wearing those footy pajamas that you should have thrown out in the fifth grade then I can't help you."

Emily giggled. She knew Alison hated her footy pajamas. "I'm not. I swear. I'm just wearing a t-shirt and underwear. That's it."

Ali's voice got really low and quiet. "Okay then, are you ready?"

"Yes. I'm ready," Emily said, still not sure if she was ready or not.

"I like to start off slow. Sometimes I like to rub my chest first, because that feels really good."

Emily felt that slickness between her legs, and squeezed her thighs together at the image of Ali, alone in her bed, touching her own breasts. She felt guilty that it turned her on, but she didn't want Alison to stop.

"Okay I'm doing it. You're right. It feels really good."

"Okay, and if Ben's doing it the right way your nipples will get really sensitive, and it will feel even better."

Emily stopped touching herself at the sound of Ben's name. "Can you please not say his name right now."

Alison's eyes darted off to the corner, deciding something, before she continued. "Okay, Em. It's just me and you then."

Emily didn't know if she liked what Alison was insinuating, but she didn't want to stop. "Okay, what next," Emily asked ready to keep going.

"Trail your hand really slowly down your stomach," Alison inhaled involuntarily at Emily's responding "Mhmm," knowing that Emily really was doing everything she said. It was driving her crazy. She reached a hand down between her own legs before thinking better of it. She crossed her legs tight, continuing, "And when you get to your underwear, slide your hand in and rub yourself." Ali paused for a moment and then said, "Are you wet?"

Emily was so wet that it was embarrassing, and she could only manage a nod. Ali's voice was in her ear, "I can't see you Emily. You have to tell me. Are you wet yet?"

"Yeah, I'm wet. I'm really wet." Somewhere inside Emily's mind she was horrified and scared that she was doing this, but a bigger more urgent part never wanted it to stop.

"Okay, that's really good, Em. You should be able to feel that there's a certain part that feels better when you -"

"I know about that part Ali - I'm not that naive."

Ali smiled. "Okay, sorry." Her voice was softer, and she was being really genuine with Emily in a way she never was with anyone else. "Just keep rubbing. You can put a finger inside and it won't hurt. If you're wet enough."

"This feels really good right now. I don't want to stop doing this."

Ali sat up, and listened intently. Not wanting to miss a single part of what was happening to Emily. She heard little moans and short breaths on the line. She strained to hear every little thing.

"Tell me what you're doing." Alison had lost all pretenses, and just wanted desperately to be able to picture Emily right now.

"I'm still rubbing myself. I can feel it's building up to something, but I can't get there." Emily sounded a little frustrated.

"It's okay. Go a little faster, and press down a little harder." Emily followed the instructions and moaned louder, no longer caring what it would sound like to Alison. Alison was breathing hard enough that she had to cover the mouthpiece with her hand when she wasn't talking.

"Okay I feel like I might almost be there. I'm almost there." Emily breathed through the line.

Alison sat frozen. She was completely and unexpectantly more turned on than she ever has been in her life by Emily Fields touching herself.

"It's not happening. It's not-what am I doing wrong?" Emily sounded really frustrated.

Alison paused for several seconds before she said. "Say my name."

Emily was shaking when she whispered, "Alison?" It sounded more like a question.

"Just say it, Emily. Say my name." Alison ordered.

"Alison." Emily said it with confidence this time, and pictured Alison. She pictured Alison was hovering above her. Touching her. The moment Emily said Alison's name out loud she knew she was reaching toward a new peak. "Alison. Oh my god. Alison. Oh fuck. Oh fuck. I'm-" Emily went silent unable to talk for a few seconds.

"You're what? Tell me." Alison demanded.

"I'm coming. I'm coming really hard. It's amazing. Oh my god. Finally." Emily was shaking and her hips were jerking outside of her control. She felt contractions as she came back down to earth; each one caused her to jerk a little until the waves of pleasure came to a complete stop. They sat on the phone silently while Emily's breathing slowed. Both not sure what to say first.

Alison broke the silence. "So now you know what it feels like. Ben won't know what hit him." Alison said Ben's name with thinly veiled distain. She felt a sharp pain in her gut, twisting and writhing, as she said it. The idea of that fumbling idiot touching Emily made her see red.

"Ali, please don't tell anyone. I'm not sure w-"

Alison cut her off, "Don't worry Em, your secrets safe with me." And then she hung up the phone.

Emily stared at the ceiling before closing her eyes with the realization: She hasn't slept with Ben yet for one reason only - she didn't want to.


	2. Emily's Second

Ali's perched on her bed, her eyes sweeping over the group seated on the floor as they eat their pizza. They're having a sleep over at her place. She always chooses her favorite to sleep in bed with her while the other girls sleep on the floor with pillows, blankets, and sleeping bags. Her eyes settle on the back of Emily's head, and she knows there's no competition this weekend as to who her favorite is.

Emily stares at the TV screen as she sets her empty plate to the side. She's barely been able to look Alison in the eyes this week after their phone call. Every time Emily dares to look her in the eye, Ali stares back with knowing smile on her face. She doesn't know if she's imagining it or not, but she would never say something about it. That would mean talking about the thing that happened, and her face burns with embarrassed heat at the memory. She's terrified other people will be able to see right through her, but so far none of the girls have questioned her strange behavior around the blonde. Her heart was pounding when her mom dropped her off at the DiLaurentis' house. She waited for Spencer to walk out of her house before knocking on the door, too afraid to be alone with Ali for any amount of time. She knew she couldn't back out of the sleepover, or Ali would know how affected she was about what happened. She hoped having a normal night might make her forget about it, and everything could go back to the way it was.

The Notebook was the movie they chose, and Emily loved The Notebook. She cried every time, and her friends always gave her a hard time about it. They all looked over at Emily when the credits rolled, and sure enough she was a blubbering mess. Aria tossed a pizza crust at her.

"Pick that up." Alison snapped at Aria. "The last thing I need is bugs in my room. I already have enough pests in here as it is."

"Hey," Spencer feigned hurt, clutching her chest. "You wound me, Ali."

Emily giggled, wiping the tears from her face. Hannah wrapped an arm around her shoulder in support.

"I think it's sweet that Emily cries during movies." Hannah looks kindly at Emily.

"Yeah, and at commercials, during weddings, on the first day of Spring, and when -" Aria couldn't complete her list before Emily spoke up to defend herself,

"I can't help it. I'm a hopeless romantic," She involuntarily glances at Ali, pushing a piece of hair behind her ear.

"How romantic was it when Ben took your V-card, Em," Ali says tauntingly, enjoying the look of panic Emily shoots her way.

"It-it was, well it was-" Emily didn't know what to say, since it hadn't really happened.

"Don't answer that, Emily. Not if you don't want to." Aria surprising comes to Emily's rescue.

"Yeah, but if you do want to then tell us because I'm dying to know," Hannah looks over at Emily with a huge smile on her face.

The smile doesn't last long when Ali interjects, "I bet you would, Hannah." The words are cruel and meant to imply that losing her virginity is something that wouldn't be happening anytime soon to Hannah. "But Emily doesn't like to kiss and tell, do you, Em?" Ali bats her eyes at Emily, causing Emily to swallow hard and avert her gaze.

About an hour and a half later the girls are changed and ready to get into their sleeping arrangements. Emily pointedly avoids eye contact, praying Ali doesn't choose her, because she doesn't think she could stand it. Lying in a bed next to her so soon after what happened on the phone.

"Hey Emily," Ali coos from across the room, patting the place next to her in the bed. Emily's kneeled down over her bag, and at the sound of her name she glances over her shoulder, seeing the gesture. She quickly looks back down at her bag, continuing to pack her toiletries. She can't think of a single thing to say to get out it, and so she zips up her bag, and walks to the bed. She slips under the covers, and keeps her arms tight to her sides. She's barely breathing she's so nervous about being in the same bed with Ali, even though the other girls were right there on the floor. Ali switches the light off, and crawls into bed, and Emily shifts a little to get comfortable. Ali waits until all the chatter and giggling subsides, making sure all the girls are asleep before whispering to Emily, "Hey, Em, are you awake?"

Emily thinks about pretending to be asleep, but the force of Ali's complete attention compels her to respond. She steels herself before turning over. Alison's eyes are wide and gentle, and Emily instantly relaxes. She knows this Ali. This Ali is sweet and kind to her. Alison reaches out to push a piece of hair behind Emily's ear, and she shifts so she's very close to Emily's face, "Do you even know how beautiful you are, Emily?" This version of Ali gives Emily the most butterflies, and she thinks, when Ali's sweet like this, she'd do anything for her. Emily doesn't know what to say, so she just shakes her head, blushing at the compliment.

"Well you are." Ali's staring at her with an intensity that Emily's never experienced before.

"I've been thinking a lot, you know, about our phone call." Alison looks Emily's face up and down, gauging her reaction. Emily freezes, her eyes wide in panic. She didn't think Ali would bring it up. She thought Ali was trying to get them back to normal, and it took her by surprise.

"Ali, I-"

"No, you don't have to apologize for it," Ali was still staring at her with an angelic expression. Her hand moved to rest on Emily's stomach, and Emily's abs flexed at the touch. Ali found the strip of bare stomach Emily's tank and shorts didn't cover and traced it with a finger. Emily inhaled sharply, and looked questioningly into Ali's eyes.

"Have you done it since?" Ali breathed out, her voice barely loud enough for Emily to hear.

Emily shook her head no, and glanced down at the girls. They were all fast asleep, and Spencer was even softly snoring.

When her eyes found Ali again, she continued her line of questioning, "Really? Once I discovered it I think I did it every night for like a month." Ali smiled at Emily, batting her eyes.

Emily didn't know if she could speak. Ali's fingertip was still drawing shapes on her bare skin, and they were talking about _that_ subject. She felt wet already, and she was so worried Ali would some how be able to tell, and would think she was some sort of perv who couldn't even handle a sleep over.

Ali's gaze was searing into Emily, but Emily couldn't get her mouth to speak.

"Have you wanted to do it again?" Ali was relentless, and Emily's heart was pounding so loud she thought somebody might hear it. She swallowed and stared at Ali for several seconds before finally admitting with a whisper, "Yeah."

Alison's eyes went dark, and she bit her lower lip before she continued, "Do you want to do it right now?"

Emily thought her heart would either stop completely or burst out of her chest. She was trapped with paralyzing desire. She nodded her head. Emily wasn't sure she could deal with this come the light of day, couldn't believe she was nodding her head, but she was. As much as she tried to not think about it all week, she had never felt something that good before. She wanted to feel it again.

"Do you want me to tell you what to do?" Alison hadn't planned this exactly, couldn't believe Emily would agree to this. How could she know that shy Emily, who could barely look at her straight on during the day, would be so sexy and willing at night? She was insanely curious to see what she could only hear last time.

Emily shook her head, "I remember." And she stared so long, immobile, looking into Alison's eyes, that Alison decided to prompt her anyway.

"Rub your chest." Emily brought her hand up at the command, and palmed her breasts over her tank top. She knew Alison could probably see how hard her nipples were through the thin fabric, and her eyes closed in embarrassment.

"No, Emily. Touch them under your shirt. It'll feel so much better."

Emily did what she was told, and when she felt her bare breasts, she squeezed harder on her nipples, and moaned involuntarily. Alison's eyes darted to the girls who were still sleeping.

"You have to be really quiet, okay? No matter how good it feels."

Emily nodded her head, and continued her attention to her breasts.

Alison stared, her attention rapt. She was completely entranced. Emily's eyes were squeezed shut, mouth hanging open slightly.

She moved her hand down slowly, still on her side facing Ali. Ali watched Emily's fingertips trace the same spot her own fingertips had earlier, and she watched as Emily's mouth tightened holding in a moan.

"Lay on your back, and open your legs." Alison eyes went almost pitch black as Emily rolled back and spread her legs as far as she had room to.

"Okay now rub yourself, but do it really slow and soft." Ali saw her hand push down past the hem of her shorts, and watched as Emily's hips thrust gently up at the first touch.

Emily could feel how wet she was. She was soaked through her shorts. She was so wet she could hear herself. Her hand stopped moving, mortified. She knew Alison heard it too.

"Don't stop." Alison was locked onto Emily's every move and sound.

"I can hear it. It's so embarrassing." Emily strained talking as quietly as she could.

Alison scooted closer to Emily. The front of her body was almost flush against the side of Emily's. She leaned in and whispered so close to Emily's ear that her lips grazed it, "Don't you want to feel good, Em? Don't you want to come?"

Emily's eyes slammed shut, and her hand went right back, unable to control herself with Ali so close. She could feel her breath on her skin. She could smell her shampoo. And she could hear her voice in her ear, whispering encouragements, "You're doing so good. Does it feel good?"

"It feels so good," Emily's back was arching, and the bed was shaking gently with the increasing speed of her motions.

Alison was watching her with complete abandon now, eyes unable to stop moving up and down her body, taking in the whole scene. She could see the frustrated look on Emily's face, and she smiled thinking about how frustrated she was the first time when she couldn't get it. She knew exactly what she needed.

"Press down harder." And she watched as Emily's tan arm flexed, the definition in her muscles appearing as she pressed down, continuing at a more frantic speed.

"Oh my God!," Emily gasped, and panic shot through Alison's body, worried she'd wake the girls. She shushed Emily, her voice harsher now, "You have to be quiet or you'll have to stop. Do you want to stop?"

Emily shook her head no, afraid to speak.

"I need more," Emily gasped quietly, "Please."

Alison thought for a second before asking, "What turns you on?"

"You." Emily was so invested in coming again that she answered without thinking.

Alison knew it already, but to hear Emily admit it like this, arching back, in her bed, struggling for pleasure, it sent her over the edge.

"Then look at me," she demanded.

Emily's eyes opened, and immediately found Alison's. She instantly began feeling the pleasure rising. Alison was staring right at her, her blue eyes, her curled lashes, her blonde hair. She was so pretty that Emily could hardly stand it. She wanted Alison to touch her, but she didn't know how to ask, so she just pretended she was. Ali was staring in amazement at Emily laid out before her. "Yes. Yes. Oh my God - it's coming. I'm-" Alison threw her hand over Emily's mouth, pushing down so she'd be quiet. Emily's motion grew frantic, and Alison watched as her back arched high, and her body convulsed, eyes never leaving Ali's. She closed them when she came down, her legs shaking, her heartbeat returning to normal.

Reality came crashing down on Emily as Alison's pretty, wide eyed stare turned to amusement - Emily's secret dancing behind her eyes, her mouth curled up, her body moving away from Emily's in the bed.

"Ali, please don't tell."

"Tell what?" Aria's head pops up from the floor, and Ali and Emily both gasp. They are farther apart now, and both fully clothed, so it doesn't look bad, but the fear in Emily's eyes are going to give them away.

Alison is staring at Aria, her eyes now glinting. She holds up her pinky finger and mouths, "Ben" at Aria.

Emily groans and presses her face into her pillow. It's not like she could come up with anything, but that? Really Alison?

Aria lets out a gasp of her own. "Emily, I'm so sorry."

Emily garbled something into her pillow that no one could understand.

Spencer wakes up rubbing her eyes. "What are you guys talking about?"

Aria starts to speak to answer Spencer's question, but Emily throws her pillow at her.

Aria shrieks, "You tell her then!"

"No body is telling any body anything." Emily's says, exasperated.

Hannah finally joins in, "Is there any pizza left?" All the girls turn to her and say, "No!" at the same time before lying back down to sleep.

A couple minutes later Emily tries to slide off the bed to go to the bathroom and clean herself up, but she feels a strong grip on her wrist, and looks at Alison inquiringly.

"Don't." Alison says in the same tone that she gives her commands in, before winking, satisfied when Emily lies back down, cheeks burning.


End file.
